Preparation method of 3-dehydroshikimic ester compound

A technology of shikimate and compounds, which is applied in the field of preparation of 3-dehydroshikimate compounds, can solve problems such as not being suitable for large-scale production, high toxicity of diazomethane, and high requirements for equipment, so as to facilitate the expansion and The effect of protection, large output and high yield

Inactive Publication Date: 2013-03-06
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the raw material used in this method relies on 3-dehydroshikimic acid prepared by biological fermentation, and its source is also limited, and diazomethane is highly toxic, and the reaction needs to be carried out at low temperature, which requires high equipment and is not suitable for large-scale Production

Method used

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  • Preparation method of 3-dehydroshikimic ester compound
  • Preparation method of 3-dehydroshikimic ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Add shikimic acid (17.4g, 0.1mol) and 150mL of anhydrous methanol into a three-necked round bottom flask, stir well, control the internal temperature of the reaction solution at 10°C, add thionyl chloride (15mL, 0.2mol) dropwise ). After the dropwise addition was completed, the internal temperature was controlled at 40° C., and the reaction was carried out for 3 hours. Concentrate to obtain a viscous liquid, which is recrystallized from ethyl acetate to obtain 14.76 g of white powdery solid methyl shikimate, yield: 78.5%.

[0025] The following is the product of step (1) 1 H NMR spectrum and MS spectrum data:

[0026] m.p.112~113℃. 1 H NMR (CD 3 COCD 3 , 400MHz) δ6.73(m, 1H, 2-H), 4.38(m, 1H, 3-H), 4.02(s, 1H, 4-OH D 2 O exchangeable), 4.00 (brs, 2H, 3, 5-OH D 2 Oexchangeable), 3.69(s, 3H, OCH 3 ), 3.85(m, 1H, 5-H), 3.68(m, 1H, 4-H), 2.64(dd, J 1 =17.6Hz,J 2 = 4.4Hz, 1H, 6α-H), 2.18(dd, J 1 =17.6Hz,J 2 =6.8Hz, 1H, 6β-H).MS(EI), m / z(%): 188(M+), 170(M + ...

Embodiment 2

[0031] (1) With embodiment 1 step (1).

[0032](2) Methyl shikimate (7.52 g, 40 mmol), IBX (13.44 g, 48 mmol) and 160 mL of tetrahydrofuran were put into a reaction flask, heated to 67° C., and stirred for 1 h. Filtration and concentration gave a light yellow solid. Recrystallized from ethyl acetate-petroleum ether to obtain 3.84 g of white fine needle crystals of methyl 3-dehydroshikimate, yield: 51.6%.

[0033] The characterization result of the product is the same as the step (2) of Example 1.

Embodiment 3

[0035] (1) With embodiment 1 step (1).

[0036] (2) Methyl shikimate (7.52g, 40mmol), IBX (13.44g, 48mmol) and 160mL of tetrahydrofuran were put into a reaction flask, heated to 50°C, and stirred for 6h. Filtration and concentration gave a light yellow solid. Recrystallized from ethyl acetate-petroleum ether to obtain 4.17 g of white fine needle crystals of methyl 3-dehydroshikimate, yield: 56.0%.

[0037] The characterization result of the product is the same as the step (2) of Example 1.

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Abstract

The invention discloses a preparation method of a 3-dehydroshikimic ester compound compound. The preparation method of the invention comprises the following steps of: carrying out an esterification reaction between shikimic acid and alcohol under the action of an acylation reagent to obtain a shikimic ester compound; and then, converting the shikimic ester compound into 3-dehydroshikimic ester compound under the action of an oxidant IBX. The invention uses a renewable non-crop biomass resource as a raw material and has the advantages of mild reaction condition, high yield, and the like, is simple to operate and easy for large-scale preparation.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a preparation method of 3-dehydroshikimate compounds. Background technique [0002] 3-Dehydroshikimate compounds are a class of hydroaromatic intermediates with important research value and application prospects. It is currently known that 3-dehydroshikimic acid (the hydrolyzate of 3-dehydroshikimate) is an important intermediate product in the biosynthesis and metabolic pathway of aromatic amino acids in microorganisms and plants, which is important for maintaining the normal development of organisms and completing metabolism. Process plays an important role. Studies in recent years have found that 3-dehydroshikimate compounds have superior antioxidant activity, and their activity is even better than commercial antioxidants such as gallic acid, propyl gallic acid, TBHQ, butylated hydroxytoluene (J. Agric. Food Chem., 2003, 51, 2753-2757), thus has potential commercial...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/313C07C69/757C07C51/373C07C62/38
Inventor 邹永陈煜魏文杨少凡孙洪宜刘现可刘新伟
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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